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Photoracemization‐Based Viedma Ripening of a BINOL Derivative

Viedma ripening is a deracemization process that has been used to deracemize a range of chiral molecules. The method has two major requirements: the compound needs to crystallize as a conglomerate and it needs to be racemizable under the crystallization conditions. Although conglomerate formation ca...

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Autores principales: Belletti, Giuseppe, Tortora, Carola, Mellema, Indradevi D., Tinnemans, Paul, Meekes, Hugo, Rutjes, Floris P. J. T., Tsogoeva, Svetlana B., Vlieg, Elias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7004087/
https://www.ncbi.nlm.nih.gov/pubmed/31663650
http://dx.doi.org/10.1002/chem.201904382
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author Belletti, Giuseppe
Tortora, Carola
Mellema, Indradevi D.
Tinnemans, Paul
Meekes, Hugo
Rutjes, Floris P. J. T.
Tsogoeva, Svetlana B.
Vlieg, Elias
author_facet Belletti, Giuseppe
Tortora, Carola
Mellema, Indradevi D.
Tinnemans, Paul
Meekes, Hugo
Rutjes, Floris P. J. T.
Tsogoeva, Svetlana B.
Vlieg, Elias
author_sort Belletti, Giuseppe
collection PubMed
description Viedma ripening is a deracemization process that has been used to deracemize a range of chiral molecules. The method has two major requirements: the compound needs to crystallize as a conglomerate and it needs to be racemizable under the crystallization conditions. Although conglomerate formation can be induced in different ways, the number of racemization methods is still rather limited. To extend the scope of Viedma ripening, in the present research we applied UV‐light‐induced racemization in a Viedma ripening process, and report the successful deracemization of a BINOL derivative crystallizing as a conglomerate. Irradiation by UV light activates the target compound in combination with an organic base, required to promote the excited‐state proton transfer (ESPT), leading thereafter to racemization. This offers a new tool towards the development of Viedma ripening processes, by using a cheap and “green” catalytic source like UV light to racemize suitable chiral compounds.
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spelling pubmed-70040872020-02-11 Photoracemization‐Based Viedma Ripening of a BINOL Derivative Belletti, Giuseppe Tortora, Carola Mellema, Indradevi D. Tinnemans, Paul Meekes, Hugo Rutjes, Floris P. J. T. Tsogoeva, Svetlana B. Vlieg, Elias Chemistry Full Papers Viedma ripening is a deracemization process that has been used to deracemize a range of chiral molecules. The method has two major requirements: the compound needs to crystallize as a conglomerate and it needs to be racemizable under the crystallization conditions. Although conglomerate formation can be induced in different ways, the number of racemization methods is still rather limited. To extend the scope of Viedma ripening, in the present research we applied UV‐light‐induced racemization in a Viedma ripening process, and report the successful deracemization of a BINOL derivative crystallizing as a conglomerate. Irradiation by UV light activates the target compound in combination with an organic base, required to promote the excited‐state proton transfer (ESPT), leading thereafter to racemization. This offers a new tool towards the development of Viedma ripening processes, by using a cheap and “green” catalytic source like UV light to racemize suitable chiral compounds. John Wiley and Sons Inc. 2019-12-12 2020-01-16 /pmc/articles/PMC7004087/ /pubmed/31663650 http://dx.doi.org/10.1002/chem.201904382 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Belletti, Giuseppe
Tortora, Carola
Mellema, Indradevi D.
Tinnemans, Paul
Meekes, Hugo
Rutjes, Floris P. J. T.
Tsogoeva, Svetlana B.
Vlieg, Elias
Photoracemization‐Based Viedma Ripening of a BINOL Derivative
title Photoracemization‐Based Viedma Ripening of a BINOL Derivative
title_full Photoracemization‐Based Viedma Ripening of a BINOL Derivative
title_fullStr Photoracemization‐Based Viedma Ripening of a BINOL Derivative
title_full_unstemmed Photoracemization‐Based Viedma Ripening of a BINOL Derivative
title_short Photoracemization‐Based Viedma Ripening of a BINOL Derivative
title_sort photoracemization‐based viedma ripening of a binol derivative
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7004087/
https://www.ncbi.nlm.nih.gov/pubmed/31663650
http://dx.doi.org/10.1002/chem.201904382
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